4-ethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole | 1305244-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-ethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole
• 英文别名: 2-[(4-Ethynylimidazol-1-yl)methoxy]ethyl-trimethylsilane
• CAS: 1305244-31-8
• 化学式: C₁₁H₁₈N₂OSi
• 分子量: 222.362
• InChiKey: HOEHGMYBMJOSCL-UHFFFAOYSA-N

物化性质

• 沸点：
  323.1±27.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-ethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole 在 三氟乙酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-4-ethynylimidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

  摘要：

  To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic) imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.018
• 作为产物：
  描述：

  1-{[2-(trimethylsilyl)ethoxy]methyl}-4-[2-(trimethylsilyl)ethynyl]-1H-imidazole 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以88%的产率得到4-ethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

  摘要：

  To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic) imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.018